2-ethyl and 2-ethylidene-19-nor-vitamin D compounds

Abstract

Biologically active 19-nor vitamin D analogs substituted at C-2 in the A-ring with an ethylidene or an ethyl group. These compounds have preferential activity on mobilizing calcium from bone and either high or normal intestinal calcium transport activity which allows their in vivo administration for the treatment of metabolic bone diseases where bone loss is a major concern. These compounds are also characterized by high cell differentiation activity.

1. A method of treating a disease characterized by an imbalance in the immune system, said disease selected from the group consisting of multiple sclerosis, diabetes mellitus, transplant rejection, lupus, and atherosclerosis, comprising administering to a patient with said disease an effective amount of a compound selected from the group consisting of
 19-nor-2α-ethyl-1α,25-dihydroxyvitamin D 3 , 
 19-nor-2β-ethyl-1α,25-dihydroxyvitamin D 3 , 
 19-nor-20(S)-2α-ethyl-1α,25-dihydroxyvitamin D 3 , 
 19-nor-20(S)-2β-ethyl-1α,25-dihydroxyvitamin D 3 , 
 19-nor-2(E)-ethylidene-1α,25-dihydroxyvitamin D 3 , 
 19-nor-2(Z)-ethylidene-1α,25-dihydroxyvitamin D 3 , 
 19-nor-2(E)-ethylidene-20(S)-1α,25-dihydroxyvitamin D 3 , and 
 19-nor-2(Z)-ethylidene-20(S)-1α,25-dihydroxyvitamin D 3 . 
 
     
     
       2. The method of  claim 1  wherein the compound is administered orally. 
     
     
       3. The method of  claim 1  wherein the compound is administered parenterally. 
     
     
       4. The method of  claim 1  wherein the compound is administered transdermally. 
     
     
       5. The method of  claim 1  wherein the compound is administered in a dosage of from about 0.01 μg to about 100 μg per day. 
     
     
       6. The method of  claim 1  wherein the compound is administered in a dosage of from about 0.1 μg to about 50 μg per day. 
     
     
       7. The method of  claim 1  wherein the compound is 19-nor-2α-ethyl-1α,25-dihydroxyvitamin D 3 . 
     
     
       8. The method of  claim 1  wherein the compound is 19-nor-2β-ethyl-1α,25-dihydroxyvitamin D 3 . 
     
     
       9. The method of  claim 1  wherein the compound is 19-nor-20(S)-2α-ethyl-1α,25-dihydroxyvitamin D 3 . 
     
     
       10. The method of  claim 1  wherein the compound is 19-nor-20(S)-2β-ethyl-1α,25-dihydroxyvitamin D 3 . 
     
     
       11. The method of  claim 1  wherein the compound is 19-nor-2(E)-ethylidene-1α,25-dihydroxyvitamin D 3 . 
     
     
       12. The method of  claim 1  wherein the compound is 19-nor-2(Z)-ethylidene-1α,25-dihydroxyvitamin D 3 . 
     
     
       13. The method of  claim 1  wherein the compound is 19-nor-2(E)-ethylidene-20(S)-1α,25-dihydroxyvitamin D 3 . 
     
     
       14. The method of  claim 1  wherein the compound is 19-nor-2(Z)-ethylidene-20(S)-1α,25-dihydroxyvitamin D 3 .